(1) Field of the Invention
This invention relates to a novel aminoalkoxystyrene which is expected to be a raw material for a functional polymer, a process for preparing the aminoalkoxystyrene, a polymer of the aminoalkoxystyrene, a process for producing the polymer, and use of the polymer.
(2) Description of the Related Art
The aminoalkoxystyrene according to the present invention is a novel compound and a process for preparing the compound is also not known.
Styrene derivatives analogous to the aminoalkoxystyrene of the present invention are known. For example, a process for preparing amino group-containing styrene derivatives has been proposed in Chemistry Letters, Japan, 1998, vol. 4, p 287-288 (Scheme 1), wherein a tosylated p-(2-hydroxyethoxy) bromobenzene, which is prepared by reacting p-bromophenol with 2-chloroethanol, followed by tosylation, is allowed to react with tributylvinyltin in the presence of a palladium catalyst to synthesize p-(2-tosyloxyethoxy)styrene, and then, the tosyloxy group of this compound is substituted by an amino compound. This process has problems for the preparation of the aminoalkoxystyrene according to the present invention because the toxic tin compound must be used in a large amount and the palladium catalyst is expensive.
Styrene derivatives having an amino group or an ammonium group in side chain or chains are widely known as an anion exchanger. The aminoalkoxystyrene according to the present invention is also expected to be useful as an anion exchanger.
As specific examples of anion exchangers, there can be mentioned strong basic anion exchangers comprising a combination of an ion exchange group including an anion exchange group such as a nitrogen- or phosphorus-containing group, for example, quaternary ammonium group and phosphonium group, with a polymeric material such as polystyrene, polyacrylate, polymethacrylate, polyvinyl alcohol or polyvinyl-allylamine. Of these, polymeric anion exchangers comprising repeating units of trimethylaminomethylstyrene are widely used.
The polymeric anion exchangers comprising repeating units of trimethylaminomethylstyrene are produced, for example, by a process wherein a styrene-divinylbenzene copolymer is reacted with chloromethyl methyl ether, and the thus-chloromethylated copolymer is reacted with trimethylamine (see, for example, Synthetic Resin Industry Technique 10, Ion Exchange Resin-Phenolic Resin, Japan, 1963, p 9-12 (Anion Exchange Resin). This process has problems such that chloromethyl methyl ether is carcinogenic, and the trimethylaminomethylstyrene structure is not stable, namely, trimethylamine and methyl group readily leave therefrom at a temperature higher than room temperature, and thus, the duration of life is short when the anion exchangers are used at a high temperature, or the anion exchangers must be used at a low temperature. Trimethylamine is readily eluted and exhales an offensive amine odor, and the amount of materials eluted from the anion exchangers is undesirably large.